The kinetics and mechanisms of aromatic halogen substitution. Part XXIII. The chlorination of N-acetylcarbazole, carbazole and related compounds

Abstract

The rates and products of chlorination of N-acetylcarbazole have been examined in acetic acid, and have been compared with results for N-acetyldiphenylamine and for related compounds. Factors of polarisability seem to be of considerable importance in determining the rate of 3-substitution. The products of chlorination of carbazole have also been estimated and the reactivity of carbazole relative to that of diphenylamine has been measured. The results establish that the influence of the resonance of the heterocyclic ring on the reactivity, though significant, is small in magnitude.